The synthesis and characterization of three homologous series of compounds exhibiting the undulated twist grain boundary smectic C* (UTGBC*) phase are reported. The chiral mesophases have been obtained using cholesterol as the chiral moiety. Cholestanol and [S]-[+]-octan-2-ol have also been used as the chiral moiety for comparitive purposes. In addition to this novel phase, cholesteric, smectic A, smectic C* and TGBA phases have also been observed. The mesophases were characterized using a combination of polarizing optical microscopy, differential scanning calorimetry, X-ray diffraction and measurement of helical pitch.